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Product Details
Chemical Properties |
clear colorless to light yellow oily liquid |
Occurrence |
Reported found in rum, coconut, raspberry, apricot, bilberry, peach, strawberry, Swiss cheese, other cheeses, butter, milk, milk powder, mutton fat, mango and nectarine. |
Uses |
Used in pharmaceutical preparations, feed additive, flavorings agent. Also used by food and flavor industries for its coconut fragrance and taste. It is also used as a reagent in the synthesis of (±)-Massoilactone (M197600); a chemical component with antibacterial activity found in volatile oils. |
Preparation |
δ-Decalactone can be prepared by peracid oxidation of 2-pentylcyclopentanone. (R)-δ-decalactone is obtained in high optical purity by starting from (R)-2- pentylcyclopentanone . Hydrogenation or fermentation of massoia lactone is also a practicable method to produce this enantiomer. A newer development for the preparation ofδ-decalactone describes a carboxylation of 1-nonen-4-ol with carbon monoxide in the presence of a homogenous palladium catalyst in an aqueous system. |
Definition |
ChEBI: A delta-lactone that is 5-valerolactone substituted by a pentyl group at position 6. |
Aroma threshold values |
Detection: 100 ppb |
Taste threshold values |
Taste characteristics at 2 ppm: waxy, coconut, lactonic, fatty, creamy, nutty and fruity. |
Synthesis Reference(s) |
The Journal of Organic Chemistry, 55, p. 462, 1990 DOI: 10.1021/jo00289a016 |
General Description |
Measurement of optical rotatory dispersion and circular dichroism of (+) 5-decanolide (tetrahydro-6-pentyl-2H-pyran-2-one) has been reported. |
Flammability and Explosibility |
Notclassified |
Synthesis |
From hexylethylene oxide and sodium malonic ester; also from decanoic acid. |
Who Evaluation |
Evaluation year: 2010 |
InChI:InChI=1/C10H18O2/c1-2-3-4-6-9-7-5-8-10(11)12-9/h9H,2-8H2,1H3/t9-/m0/s1
-
In this study, we reported a photo-induc...
The invention relates to a synthesis pro...
Two cis-β-MnIIISALPN catalysts were synt...
The conversion of saturated fatty acids ...
2-pentyl-cyclopentanone
δ-decanolactone
(+/-)-δ-decanolactone
Conditions | Yield |
---|---|
With
dihydrogen peroxide;
scandium(III) tris[bis(perfluorooctanesulfonyl)imide];
In
various solvent(s);
at 20 ℃;
for 5h;
Title compound not separated from byproducts.;
|
|
With
dihydrogen peroxide;
lithium hydroxide;
In
Ethyl propionate;
at 100 ℃;
for 6h;
Heating / reflux;
|
|
With
dihydrogen peroxide;
lithium hydroxide;
In
water; Ethyl propionate;
at 110 ℃;
for 6h;
Heating / reflux;
|
|
With
dihydrogen peroxide;
sodium tert-pentoxide;
In
water; Ethyl propionate;
at 110 ℃;
for 6h;
Heating / reflux;
|
|
With
dihydrogen peroxide;
lithium hydroxide;
In
tert-Amyl alcohol; water;
at 110 ℃;
for 6h;
Heating / reflux;
|
|
With
dihydrogen peroxide;
sodium hydrogencarbonate;
In
water; Ethyl propionate;
at 110 ℃;
for 6h;
Heating / reflux;
|
|
With
dihydrogen peroxide;
sodium hydrogencarbonate;
In
tert-Amyl alcohol; water;
at 110 ℃;
for 6h;
Heating / reflux;
|
|
With
dihydrogen peroxide;
magnesium 2-ethylhexanoate;
In
water; Ethyl propionate;
at 110 ℃;
for 6h;
Heating / reflux;
|
|
With
dihydrogen peroxide;
sodium hydroxide;
In
tert-Amyl alcohol; water;
at 110 ℃;
for 6h;
Heating / reflux;
|
|
With
dihydrogen peroxide;
lithium bromide;
In
water; Ethyl propionate;
at 110 ℃;
for 6h;
Heating / reflux;
|
|
With
dihydrogen peroxide;
potassium acetate;
In
water; Ethyl propionate;
at 110 ℃;
for 6h;
Heating / reflux;
|
|
With
dihydrogen peroxide;
sodium 2,2,2-trifluoroacetate;
In
water; Ethyl propionate;
at 110 ℃;
for 6h;
Heating / reflux;
|
|
With
dihydrogen peroxide;
sodium 2-ethylhexanoic acid;
In
water; Ethyl propionate;
at 110 ℃;
for 6h;
Heating / reflux;
|
|
With
dihydrogen peroxide;
lithium acetate;
In
water; chlorobenzene;
at 110 ℃;
for 6h;
Reactivity;
Heating / reflux;
|
|
With
dihydrogen peroxide;
lithium acetate;
In
1,4-dioxane; water;
at 110 ℃;
for 6h;
Reactivity;
Heating / reflux;
|
|
With
dihydrogen peroxide;
lithium acetate;
In
Isopropyl acetate; water;
at 110 ℃;
for 6h;
Reactivity;
Heating / reflux;
|
|
With
dihydrogen peroxide;
lithium acetate;
In
water; Ethyl propionate;
at 110 ℃;
for 6h;
Heating / reflux;
|
|
With
dihydrogen peroxide;
lithium acetate;
In
tert-Amyl methyl ether; water;
at 110 ℃;
for 6h;
Reactivity;
Heating / reflux;
|
|
With
dihydrogen peroxide;
calcium carbonate;
In
water; Ethyl propionate;
at 110 ℃;
for 6h;
Heating / reflux;
|
|
With
dihydrogen peroxide;
sodium peroxide;
In
water; Ethyl propionate;
at 110 ℃;
for 6h;
Heating / reflux;
|
|
With
dihydrogen peroxide;
Na(polyacrylate);
In
water; Ethyl propionate;
at 110 ℃;
for 6h;
Heating / reflux;
|
|
With
dihydrogen peroxide;
lithium pentane-2,4-dionate;
In
water; Ethyl propionate;
at 110 ℃;
for 6h;
Heating / reflux;
|
|
With
dihydrogen peroxide;
lithium carbonate;
In
water; Ethyl propionate;
at 110 ℃;
for 6h;
Heating / reflux;
|
|
With
dihydrogen peroxide;
barium carbonate;
In
water; Ethyl propionate;
at 110 ℃;
for 6h;
Heating / reflux;
|
non-1-en-4-ol
carbon monoxide
3-methyl-5-pentyldihydrofuran-2(3H)-one
1-decanoic acid
(+/-)-δ-decanolactone
Conditions | Yield |
---|---|
carbon monoxide;
triphenylphosphine; palladium dichloride;
In
toluene;
at 80 ℃;
for 2h;
under 7500.75 Torr;
non-1-en-4-ol;
tin(ll) chloride;
In
water; toluene;
at 80 - 100 ℃;
for 18h;
Product distribution / selectivity;
|
65% |
decan-1,5-diol
6-pentyl-tetrahydro-2H-pyran-2-ol
3-Benzenesulfinyl-6-pentyl-tetrahydro-pyran-2-one
5-Acetoxydecannitril
decanamide
cis-6-pentyl-2-(phenylthio)tetrahydropyran
trans-6-pentyl-2-(phenylthio)tetrahydropyran
Non-3-en-2-on
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